US5334443A - Substrate with adhesion promoting film comprising vinyl chloride polymer plasticized with polyketone - Google Patents
Substrate with adhesion promoting film comprising vinyl chloride polymer plasticized with polyketone Download PDFInfo
- Publication number
- US5334443A US5334443A US07/845,120 US84512092A US5334443A US 5334443 A US5334443 A US 5334443A US 84512092 A US84512092 A US 84512092A US 5334443 A US5334443 A US 5334443A
- Authority
- US
- United States
- Prior art keywords
- vinyl chloride
- polyketone
- chloride polymer
- adhesion promoting
- film
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06N—WALL, FLOOR, OR LIKE COVERING MATERIALS, e.g. LINOLEUM, OILCLOTH, ARTIFICIAL LEATHER, ROOFING FELT, CONSISTING OF A FIBROUS WEB COATED WITH A LAYER OF MACROMOLECULAR MATERIAL; FLEXIBLE SHEET MATERIAL NOT OTHERWISE PROVIDED FOR
- D06N3/00—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof
- D06N3/04—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof with macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06N3/06—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof with macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds with polyvinylchloride or its copolymerisation products
- D06N3/065—PVC together with other resins except polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/12—Bonding of a preformed macromolecular material to the same or other solid material such as metal, glass, leather, e.g. using adhesives
- C08J5/124—Bonding of a preformed macromolecular material to the same or other solid material such as metal, glass, leather, e.g. using adhesives using adhesives based on a macromolecular component
- C08J5/128—Adhesives without diluent
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
- C08L27/02—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L27/04—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms
- C08L27/06—Homopolymers or copolymers of vinyl chloride
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D127/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers
- C09D127/02—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment
- C09D127/04—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms
- C09D127/06—Homopolymers or copolymers of vinyl chloride
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L73/00—Compositions of macromolecular compounds obtained by reactions forming a linkage containing oxygen or oxygen and carbon in the main chain, not provided for in groups C08L59/00 - C08L71/00; Compositions of derivatives of such polymers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/28—Web or sheet containing structurally defined element or component and having an adhesive outermost layer
- Y10T428/2804—Next to metal
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/28—Web or sheet containing structurally defined element or component and having an adhesive outermost layer
- Y10T428/2852—Adhesive compositions
- Y10T428/2878—Adhesive compositions including addition polymer from unsaturated monomer
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/10—Scrim [e.g., open net or mesh, gauze, loose or open weave or knit, etc.]
- Y10T442/102—Woven scrim
- Y10T442/172—Coated or impregnated
Definitions
- substrates e.g., an open weave substrate, e.g., one formed of polyester, polyamide, or a combination thereof
- a plasticized vinyl chloride polymer to form a coated fabric which can be used as single-ply roofing, in air ducts, as a pond liner, as a tarpaulin, as a mining belt, and the like.
- a prepolymer containing at least 2% of isocyanate groups e.g., U.S. Pat. No. 4,806,414.
- This approach has been criticized, for example, as posing a potential health danger to persons coming in contact with the adhesive (see U.S. Pat. No. 4,806,414 at Col. 1, lines 35-39).
- U.S. Pat. No. 3,808,288 describes a pressure sensitive adhesive containing an epichlorohydrin polymer and a selected polyketone resin which is described as being the condensation polymer of one or more types of ketone with a lower aliphatic aidehyde. This composition can be used to form a pressure sensitive adhesive on a number of flexible backings (see Col. 2, lines 24-40).
- a carbon monoxide-propylene copolymer preferably in liquid form, can effectively plasticize a vinyl chloride polymer (see U.S. Pat. No. 5,109,047, which is incorporated herein by reference).
- a preferred copolymer of this type is formed by polymerizing the carbon monoxide and propylene in an essentially ketone solvent to form a product substantially free of carboxylic ester and ether linkages or, if carboxylic acid end groups are desired, conducting the polymerization in a ketone/water solvent medium (see U.S. Pat. No. 5,270,441, which is also incorporated herein by reference).
- the present invention relates to a laminate of substrate, such as an open weave substrate, and an adhesion promoting film which, preferably, is prepared via the plastisol method comprising mixing a dispersion grade vinyl chloride polymer which has been plasticized with a liquid carbon monoxide-propylene copolymer.
- the aforementioned construction is useful, for example, as a coated fabric for a variety of end-uses as mentioned above.
- the preferred open weave substrate which can be used herein is known to persons of ordinary skill in the art and includes open weave fabrics formed of such polymers as the polyesters (e.g., polyethylene terephthalate or polybutylene terephthalate), the polyamides (e.g., nylon 6, nylon 66, nylon 12).
- the present invention is also applicable to bonding other substrates to one another.
- Examples 3-4 show use of the invention with polyester films.
- the subcombination of such laminates i.e., a coated substrate, such as a coated film, yarn, open weave fabric, metals (such as copper or aluminum, which might be useful as a substrate in coil coating applications), and the like
- Such a combination comprises: (a) the desired substrate; and (b) the film of vinyl chloride polymer and carbon monoxide propylene polyketone plasticizer.
- the film (b) allows for the lamination of (a) and (b) to other structures.
- the vinyl chloride polymer which forms the major component (e.g., from about 30 wt % to about 70 wt %) of the adhesion promoting film can be selected from known homopolymers of vinyl chloride monomer or known copolymers of vinyl chloride monomer with one or more ethylenically unsaturated monomers. Either suspension or emulsion grade vinyl chloride polymer resin can be chosen for use depending upon the method of fabrication chosen.
- the carbon monoxide-propylene copolymer (or polyketone) which functions as a plasticizer (at from about 70% to about 30%, of the blend of polymer and polyketone), for the aforementioned vinyl chloride polymer in the adhesion promoting film used herein can have a molecular weight of from about 400 to about 10,000 depending upon whether the adhesion promoting film is to be prepared by either the calendering/extrusion method or by the plastisol method. In the former case, the molecular weight can range from about 1,000 to about 10,000 so that the blend of carbon monoxide-propylene polyketone and vinyl chloride polymer is a very viscous fluid to viscous semi-solid. If a more fluid plastisol is desired, the molecular weight will be from about 400 to about 1,000 so that a fluid to viscous fluid is produced with a viscosity of from about 300 to about 50,000 cps.
- an optional top coat of an acrylic polymer can be applied to one or both sides of the coated fabric-adhesion promoting film structure, but this is not necessary.
- Such a top coat is routinely applied, for health and safety reasons, to coated fabrics which contain an isocyanate-containing binder in addition to conventional films of plasticized vinyl chloride polymer and open weave fabric.
- the viscosity evaluation tests were performed (LVT, 12 rpm, spindle No. 4) on each sample with the viscosity values for Sample A being 21,900 cps and 22,100 cps, respectively, and the viscosity values for Sample B being 36,300 cps and 36,500 cps, respectively.
- Plastisol formulations for each were fabricated as follows:
- the plastisol viscosities (LVT, 12 rpm, spindle No. 4) were 20,850 cps and 23,000 cps, respectively.
- DOP dioctyl phthalate
- the above experiment demonstrates the permanency of the carbon monoxide-propylene copolymer as a plasticizer.
- the carbon monoxide-propylene copolymer appears to retard the extraction of phthalate plasticizer from the film coating by hexane.
- Example 1 the low molecular weight carbon monoxide/propylene copolymer of Example 1 (Sample A) was used as a plasticizer in the following formulation:
- This Example demonstrates the use of the plastisol method to laminate films of polyester (Mylar brand).
- the above formulation was coated (about 6 mils) on top of a polyester film and was then fused at 180° C. for fifteen minutes. The adhesion of the fused film to the polyester was good. Then, another polyester film was placed on top of the fused film in the previously formed polyester/film laminate followed by compression molding at 180°/190° C. for five minutes. The adhesion of the fused film to both polyester films was good.
- the ingredients in the above-described formulations were mixed together in separate 4 ounce glass jars and then passed through a laboratory two roll mill until a homogeneous plastisol was formed.
- the two plastisol formulations were then each coated onto two polyethylene terephthalate open weave fabrics in a two inch wide and three mil thick film.
- the plastisol coatings were pregelled at 150° C. for two minutes.
- the facing plastisol surfaces of the two respective plastisol/fabric laminates for each formulation A and B were contacted to each other (or "kissed") to form a laminate comprising two final laminated fabrics with an intermediate layer of gelled plastisol between the fabrics.
- the two final laminates were placed in a compression press under 6,000 pounds per square inch pressure and were heated for two minutes at 190° C.
Abstract
Description
______________________________________ Weight (grams) Ingredient Wt % A B ______________________________________ PVC resin (GEON 121 brand) 52.6 50 50 Sample A 20.0 19 -- Sample B 20.0 -- 19 Dioctyl phthalate (DOP) 21.0 22.1 22.1 Epoxidized soyabean oil 5.0 5.3 5.3 ______________________________________
______________________________________ Parameter Measured Tie Coat* A B ______________________________________ Initial Weight (gm) 0.73 0.75 0.83 Weight After Extraction (gm) 0.46 0.68 0.76 Theoretical Loss of DOP (%) 40.3 22 22 Actual Loss (%) 37 9.3 9.3 ______________________________________ *commercial tie coat: 54% PVC; 40% diisononyl phthalate (DINP) plasticizer; 1.5% Intercide ABF arseniccontaining biocide; 3.0% filler; and 1.5% stabilizer.
______________________________________ Parts by Ingredient Weight (grams) ______________________________________ PVC Resin (GEON 102 EP) 32 CO/Propylene Copolymer 20 Tin mercaptide stabilizer 1.0 Phosphite heat stabilizer (SYNPRON 1535) 0.2 Epoxidized soyabean oil 3.0 ______________________________________
______________________________________ Time (min) Temp. (°C.) Torque ______________________________________ 0 160 -- 2 148 2000 4 162 1320 6 163 1245 10 161 1200 ______________________________________
______________________________________ RPM Viscosity (cps) ______________________________________ 12 4600 30 4600 60 4550/4640 ______________________________________
______________________________________ Ingredient Percentage by Weight (grams) ______________________________________ PVC Resin (GEON 121) 42 CO/Propylene Copolymer 50 Tin mercaptide 3 Epoxidized soyabean oil 5 ______________________________________
______________________________________ Ingredient SAMPLE A SAMPLE B ______________________________________ PVC Resin (GEON 121) 30 g 30 g Dioctyl Phthalate 13 g 22 g CO/Propylene Copolymer 9 g 0 g Barium/Cadmium Stabilizer 0.9 g 0.9 g CaCO.sub.3 Filler 3 g 3 g Titanium Dioxide 0.6 g 0.6 g ______________________________________
Claims (8)
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/845,120 US5334443A (en) | 1990-10-10 | 1992-03-03 | Substrate with adhesion promoting film comprising vinyl chloride polymer plasticized with polyketone |
PCT/US1993/001831 WO1993017861A1 (en) | 1992-03-03 | 1993-02-26 | Substrate with adhesion promoting film comprising vinyl chloride polymer plasticized with polyketone |
EP93906272A EP0705166A1 (en) | 1992-03-03 | 1993-02-26 | Substrate with adhesion promoting film comprising vinyl chloride polymer plasticized with polyketone |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/595,060 US5109047A (en) | 1990-10-10 | 1990-10-10 | Plasticization of polyvinyl chloride with carbon monoxide-propylene copolymer |
US07/845,120 US5334443A (en) | 1990-10-10 | 1992-03-03 | Substrate with adhesion promoting film comprising vinyl chloride polymer plasticized with polyketone |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US07/595,060 Continuation-In-Part US5109047A (en) | 1990-10-10 | 1990-10-10 | Plasticization of polyvinyl chloride with carbon monoxide-propylene copolymer |
Publications (1)
Publication Number | Publication Date |
---|---|
US5334443A true US5334443A (en) | 1994-08-02 |
Family
ID=25294454
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US07/845,120 Expired - Fee Related US5334443A (en) | 1990-10-10 | 1992-03-03 | Substrate with adhesion promoting film comprising vinyl chloride polymer plasticized with polyketone |
Country Status (3)
Country | Link |
---|---|
US (1) | US5334443A (en) |
EP (1) | EP0705166A1 (en) |
WO (1) | WO1993017861A1 (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6239250B1 (en) | 1999-04-16 | 2001-05-29 | Air Products And Chemicals, Inc. | Hot melt adhesives produced from linear alternating polyketones |
US20060252320A1 (en) * | 2005-05-06 | 2006-11-09 | Cooley, Incorporated | Method of forming a PVC scrim fabric laminate having superior scuff and abrasion resistance |
US11505944B2 (en) * | 2018-04-03 | 2022-11-22 | Raven Engineered Films, Inc. | Composite shingle including polyketone |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20040058112A1 (en) * | 2002-09-25 | 2004-03-25 | Ats Products, Inc. | Method for making tubular articles |
GB2448702A (en) * | 2007-04-24 | 2008-10-29 | Louis Cevoli | System for installing a pond liner |
Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3780140A (en) * | 1971-08-06 | 1973-12-18 | Du Pont | Ethylene/carbon monoxide polymer compositions |
US3808288A (en) * | 1971-12-06 | 1974-04-30 | Kendall & Co | Pressure-sensitive adhesives based on epihalohydrin polymer and polyketone resins |
DE2433722A1 (en) * | 1974-07-13 | 1976-01-29 | Henkel & Cie Gmbh | PROCESS FOR IMPROVED THERMOPLASTIC HOT DEFORMING OF POLYVINYL CHLORIDE |
US3945876A (en) * | 1972-04-07 | 1976-03-23 | E. I. Dupont De Nemours & Company | Bonding with polyisocyanates |
US4795773A (en) * | 1987-09-22 | 1989-01-03 | Shell Oil Company | Plasticized composition and method of production |
US4806414A (en) * | 1985-09-04 | 1989-02-21 | Akzo Nv | Composite material |
US4820578A (en) * | 1988-04-28 | 1989-04-11 | Shell Oil Company | Polyketone roofing membranes |
US4871618A (en) * | 1987-12-04 | 1989-10-03 | Shell Oil Company | Laminar structures prepared with polyketone structural adhesives |
US4880904A (en) * | 1987-12-04 | 1989-11-14 | Shell Oil Company | Polyketone-based structural adhesive |
US5087664A (en) * | 1985-08-19 | 1992-02-11 | Mitsubishi Kasei Vinyl Company | Plastisol composition and undercoating material |
US5109047A (en) * | 1990-10-10 | 1992-04-28 | Akzo Nv | Plasticization of polyvinyl chloride with carbon monoxide-propylene copolymer |
-
1992
- 1992-03-03 US US07/845,120 patent/US5334443A/en not_active Expired - Fee Related
-
1993
- 1993-02-26 EP EP93906272A patent/EP0705166A1/en not_active Withdrawn
- 1993-02-26 WO PCT/US1993/001831 patent/WO1993017861A1/en not_active Application Discontinuation
Patent Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3780140A (en) * | 1971-08-06 | 1973-12-18 | Du Pont | Ethylene/carbon monoxide polymer compositions |
US3808288A (en) * | 1971-12-06 | 1974-04-30 | Kendall & Co | Pressure-sensitive adhesives based on epihalohydrin polymer and polyketone resins |
US3945876A (en) * | 1972-04-07 | 1976-03-23 | E. I. Dupont De Nemours & Company | Bonding with polyisocyanates |
DE2433722A1 (en) * | 1974-07-13 | 1976-01-29 | Henkel & Cie Gmbh | PROCESS FOR IMPROVED THERMOPLASTIC HOT DEFORMING OF POLYVINYL CHLORIDE |
US5087664A (en) * | 1985-08-19 | 1992-02-11 | Mitsubishi Kasei Vinyl Company | Plastisol composition and undercoating material |
US4806414A (en) * | 1985-09-04 | 1989-02-21 | Akzo Nv | Composite material |
US4795773A (en) * | 1987-09-22 | 1989-01-03 | Shell Oil Company | Plasticized composition and method of production |
US4871618A (en) * | 1987-12-04 | 1989-10-03 | Shell Oil Company | Laminar structures prepared with polyketone structural adhesives |
US4880904A (en) * | 1987-12-04 | 1989-11-14 | Shell Oil Company | Polyketone-based structural adhesive |
US4820578A (en) * | 1988-04-28 | 1989-04-11 | Shell Oil Company | Polyketone roofing membranes |
US5109047A (en) * | 1990-10-10 | 1992-04-28 | Akzo Nv | Plasticization of polyvinyl chloride with carbon monoxide-propylene copolymer |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6239250B1 (en) | 1999-04-16 | 2001-05-29 | Air Products And Chemicals, Inc. | Hot melt adhesives produced from linear alternating polyketones |
US20060252320A1 (en) * | 2005-05-06 | 2006-11-09 | Cooley, Incorporated | Method of forming a PVC scrim fabric laminate having superior scuff and abrasion resistance |
US11505944B2 (en) * | 2018-04-03 | 2022-11-22 | Raven Engineered Films, Inc. | Composite shingle including polyketone |
Also Published As
Publication number | Publication date |
---|---|
WO1993017861A1 (en) | 1993-09-16 |
EP0705166A4 (en) | 1995-01-10 |
EP0705166A1 (en) | 1996-04-10 |
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Owner name: AKZO N.V., A CORP. OF THE NETHERLANDS, NETHERLANDS Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNORS:GOSWAMI, JAGADISH C.;ALESSIO, GERALD R.;REEL/FRAME:006094/0590 Effective date: 19920303 |
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Free format text: PATENT EXPIRED FOR FAILURE TO PAY MAINTENANCE FEES (ORIGINAL EVENT CODE: EXP.); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY |
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Effective date: 20020802 |